ChemInform Abstract: Enantioselective Synthesis of 4-Aminocyclopent-2-ene-1-one from Tricyclo[5.2.1.02,6]decenyl Enaminones.

✍ Scribed by N. G. RAMESH; A. J. H. KLUNDER; B. ZWANENBURG

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199822034

✦ Synopsis

Enantioselective Synthesis of 4-Aminocyclopent-2-ene-1-one from Tricyclo[5.2.1.0 2,6 ]decenyl Enaminones.

-The enantioselective synthesis of hitherto unknown 4-aminocyclopent-2-en-1-one (VI) involves reaction of enamine (III) with lithium liquid ammonia which not only results in reduction of the enamine but simultaneously removes the chiral auxiliary leading to the formation of β-amino ketone (IV) as major diastereomer. The following retro-Diels-Alder reaction of the diastereomeric mixture occurs with no significant racemization giving the cyclopentane derivative (V). Finally, the title compound (VI) is easily achieved from (V) by hydrolysis. -(RAMESH,